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Road cycling routes

South East England

Longwood Dean Lane Tree Tunnel – Old Winchester Hill loop from Medstead

Road cycling routes

South East England

Longwood Dean Lane Tree Tunnel – Old Winchester Hill loop from Medstead

Moderate

14

riders

Longwood Dean Lane Tree Tunnel – Old Winchester Hill loop from Medstead

03:37

75.8km

800m

Road cycling

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride. The starting point of the route is accessible with public transport.

Last updated: March 19, 2026

Tips

The surface for a segment of your route may not be suitable

Some segments of your route comprise a surface that may not be suitable for your chosen sport.

After 45.0 km for 213 m

Waypoints

A

Start point

Bus stop

Get Directions

1

16.4 km

Sunset View of the River Itchen

Highlight • River

2

17.7 km

Cheriton Village

Highlight • Historical Site

Cheriton is a stunning Hampshire village. It houses a beautiful old church and Cheriton Post Office and Stores, which is a great place to stop and restock refreshments.

Tip by

3

22.7 km

View of Wildflower Fields in South Downs National Park

Highlight • Viewpoint

Nice place to stop if you need a break. Very tranquil.

Tip by

4

25.0 km

Longwood Dean Lane

Highlight (Segment) • Cycleway

This is a stunning tree-lined road where the trees arch toward each other, forming a natural canopy overhead as you cycle through.

Tip by

5

27.2 km

Longwood Dean Lane Tree Tunnel

Highlight • Viewpoint

Longwood Dean Lane is a beautiful back country lane just east of Owslebury. It is a stunning tree lined lane with the glimpses of open country in places. It’s a …

Tip by

45.1 km

Boarhuts Copse

Forest

7

45.9 km

The Old Forge Tearoom

Highlight • Cafe

Friendly helpful staff, good food at reasonable prices. Fantastic cake and some of the best coffee in Hampshire.

Tip by

8

53.7 km

Old Winchester Hill

Highlight (Segment) • Historical Site

Recently surfaced road at the top makes cycling there much smoother. There is a coffee van across the road from the car park most days.

Tip by

9

55.3 km

View from Old Winchester Hill

Highlight • Historical Site

The road offers some great views over the adjacent Old Winchester Hill National Nature Reserve, Iron Age hillfort and the surrounding countryside.

Tip by

59.5 km

Lippen Wood

Forest

B

75.8 km

End point

Bus stop

Way Types & Surfaces

Way Types

71.6 km

2.10 km

1.82 km

186 m

152 m

Surfaces

56.9 km

18.8 km

186 m

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (210 m)

Lowest point (40 m)

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Weather

Powered by Foreca

Wednesday 27 May

28°C

14°C

39 %

Additional weather tips

Max wind speed: 21.0 km/h

to get more detailed weather forecasts along your route

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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